Our official English website, www.x-mol.net, welcomes your
feedback! (Note: you will need to create a separate account there.)
Synthesis of Aromatic and Aliphatic Di-, Tri-, and Tetrasulfonic Acids
Synlett ( IF 1.7 ) Pub Date : 2020-03-17 , DOI: 10.1055/s-0039-1691745 Jens Christoffers 1 , Mathias S. Wickleder 2
Synlett ( IF 1.7 ) Pub Date : 2020-03-17 , DOI: 10.1055/s-0039-1691745 Jens Christoffers 1 , Mathias S. Wickleder 2
Affiliation
|
Oligosulfonic acids are promising linker compounds for coordination polymers and metal-organic frameworks, however, compared to their carboxylic acid congeners, often not readily accessible by established synthetic routes. This Account highlights the synthesis of recently developed aromatic and aliphatic di-, tri- and tetrasulfonic acids. While multiple electrophilic sulfonations of aromatic substrates are rather limited, the nucleophilic aromatic substitution including an intramolecular variant, the Newman–Kwart rearrangement, allows the flexible introduction of up to four sulfur-containing moieties at an aromatic ring. Sulfonic acids are then accessed by oxidation of thiols, thioethers, or thioesters either directly with hydrogen peroxide or in two steps with chlorine (generated in situ from N-chlorosuccinimide/hydrochloric acid) to furnish sulfochlorides which are subsequently hydrolyzed. In the aliphatic series, secondary alcohols as starting materials are converted into thioethers, thioesters, or thiocarbonates by nucleophilic substitutions, which are also subsequently oxidized to furnish sulfonic acids. 1 Introduction 2 Electrophilic Aromatic Substitution 3 Nucleophilic Aromatic Substitution 3.1 Intermolecular SNAr 3.2 Intermolecular with Subsequent Oxidation 3.3 Intramolecular with Subsequent Oxidation 4 Nucleophilic Aliphatic Substitution with Subsequent Oxidation 5 Oxidation 5.1 Oxidation of Thiocarbonates 5.2 Oxidation of Thioethers 5.3 Oxidation of Thioesters 6 Thermolysis of Neopentylsulfonates 7 Functionalization via Diazonium Ions 8 Conclusion
中文翻译：
芳香族和脂肪族二磺酸、三磺酸和四磺酸的合成
低聚磺酸是用于配位聚合物和金属-有机骨架的有前途的接头化合物，然而，与其羧酸同类物相比，通常不易通过已建立的合成路线获得。本报告重点介绍了最近开发的芳香族和脂肪族二磺酸、三磺酸和四磺酸的合成。虽然芳香底物的多重亲电磺化相当有限，但亲核芳香取代包括分子内变体 Newman-Kwart 重排，允许在芳香环上灵活引入多达四个含硫部分。然后通过硫醇、硫醚、或硫酯直接用过氧化氢或分两步用氯（由 N-氯代琥珀酰亚胺/盐酸原位生成）以提供随后水解的硫氯化物。在脂肪族系列中，作为起始原料的仲醇通过亲核取代转化为硫醚、硫酯或硫代碳酸酯，随后它们也被氧化以提供磺酸。1 引言 2 亲电芳香取代 3 亲核芳香取代 3.1 分子间 SNAr 3.2 分子间与随后的氧化 3.3 分子内与随后的氧化 4 亲核脂肪取代与随后的氧化 5.1 氧化硫醚的 5.1 氧化硫醚的氧化
更新日期：2020-03-17
中文翻译：
芳香族和脂肪族二磺酸、三磺酸和四磺酸的合成
低聚磺酸是用于配位聚合物和金属-有机骨架的有前途的接头化合物，然而，与其羧酸同类物相比，通常不易通过已建立的合成路线获得。本报告重点介绍了最近开发的芳香族和脂肪族二磺酸、三磺酸和四磺酸的合成。虽然芳香底物的多重亲电磺化相当有限，但亲核芳香取代包括分子内变体 Newman-Kwart 重排，允许在芳香环上灵活引入多达四个含硫部分。然后通过硫醇、硫醚、或硫酯直接用过氧化氢或分两步用氯（由 N-氯代琥珀酰亚胺/盐酸原位生成）以提供随后水解的硫氯化物。在脂肪族系列中，作为起始原料的仲醇通过亲核取代转化为硫醚、硫酯或硫代碳酸酯，随后它们也被氧化以提供磺酸。1 引言 2 亲电芳香取代 3 亲核芳香取代 3.1 分子间 SNAr 3.2 分子间与随后的氧化 3.3 分子内与随后的氧化 4 亲核脂肪取代与随后的氧化 5.1 氧化硫醚的 5.1 氧化硫醚的氧化
京公网安备 11010802027423号